CARBOHYDARTES NOTES FROM BOOK
as ketones.
 Carbohydrates are the most abundant organic
compounds in the plant world.
 They act as a storehouse of chemical energy
(glucose, starch, glycogen).
 Are components of supportive structures in
plants, crustacean shells, and connective tissues
in animals;
 And are essential components nucleic acids.
 Carbohydrates account for approx3/4 of the dry
weight of plants.
 Animals including humans get their
carbohydrates by eating plants do not store
much of what they consume.
 Less than 1% the body weight of animals is
made up of carbohydrates.
 Carbohydrate means hydrate of carbon.
 derives from the formula Cn (H2O) m.Not all
carbohydrates however have this general
formula.
 Two examples of carbohydrates with this
general molecular formula that can be written
alternatively as hydrates of carbon are:
o Glucose (blood sugar) C6H12O6
o Sucrose (table sugar) C12H22O11
 At the molecular level,carbohydrates are
polyhydroxy aldehydes, polyhydroxy ketones,
compounds that yield them their hydrolysis.
 The simpler members of the carbohydrate
family often referred to us saccharides because
of their sweet taste.
 Saccharides in Latin saccharum, sugar.
 Carbohydrates are classified as
monosaccharides, oligosaccharides, or
polysaccharides in depending on the number of
simple sugars they contain
 Monosaccharides have the general formula
C_H_2nO_n with one of the carbons being the
carbonyl group of either an aldehyde or a
ketone.
 The most common monosaccharides have 3 to
9 carbon atoms
 The suffix - oseindicates that a molecule is a
carbohydrate,
 The prefixes tri -, tetr-, pent-, and so forth
indicate the number carbon atoms in the chain.
 Monosaccharides containing an aldehyde
group are classified as aldoses
 Those containing a ketone group are classified
 There are only two trioses the aldotriose
glyceraldehyde and ketotriose
dihydroxyacetone.
 Chemists commonly used two-dimensional
representation called Fischer projections
o Two-dimensional representations
showing the configuration of a
stereocenter
o ; horizontal lines represent bond
projecting forward from the
stereocenter
o and vertical lines represent bonds
projecting toward the rear
 D, L system proposed by Emil Fischer in 1891.
 He assigned the dextrorotatory enantiomer the
following configuration and named it D-
glyceraldehyde. He named its enantiomer L-
glyceraldehyde.
 In 1952, scientist proved that his assignment D,
L - configuration to the in enantiomers of
glyceraldehyde was correct.
 D-glyceraldehyde and L-glyceraldehyde serve
as reference points for the assignment of
relative configurations other aldoses and
ketoses.
 The reference point is the penultimate carbon -
that is, the next to the last carbon on the chain
 D-monosaccharide the same configuration it's
penultimate carbon as D-glyceraldehyde (its -
OH group is on the right)
 L-monosaccharide has the same configuration
at penultimate carbon as L-glyceraldehyde (its
-OH group is on the left).
 Each name consists of 3 parts:
o The D specifies the configuration at the
stereocenter farthest from the carbonyl
group.
o Prefixes such as rib-, arabin-, and gluc-
specify the configuration of all other
stereocenters in the monosaccharide
relative to one another.
o The suffix -ose indicates that the
compound is a carbohydrate.
 The three most abundant hexoses in the
biological world are D-glucose, D-galactose,
and D-fructose.
  The first two are D-aldohexoses; the third is a
D-2-ketohexose.
 Glucose, by far the most abundant of the three,
is also known as dextrose because it is
dextrorotatory.
 Other names for this monosaccharide include
grape sugar and blood sugar.
 Human blood normally contains 65–110 mgof
glucose/100 mL of blood.
 Amino sugars - monosaccharides in which an –
OH group is replaced with an -NH2 group
D. Amino Sugars
 Amino sugars contain an —NH, group in place
of an OH group.
 Onlythree amino sugars are common in nature:
D-glucosamine, D-mannosamine,
 and D-galactosamine.
 N-Acetyl-D-glucosamine, a derivative of D-
glucosamine, is a component of many
polysaccharides, including connective tissue
such as cartilage.
 It is also a component of chitin, the hard, shell-
like exoskeleton of lobsters, crabs, shrimp, and
other shellfish.
 Several other amino sugars are components of
naturally-occurring antibiotics.
E. Physical Properties of Monosaccharides
 Monosaccharides are colorless, crystalline
solids. Because hydrogen bonding is possible
between their polar –OH groups and water, all
monosaccharides are very soluble in water.
 They are only slightly soluble in ethanol and are
insoluble in nonpolar solvents such as diethyl
ether, dichloromethane, and benzene.
 We saw that aldehydes and ketonesreact with
alcohols to: form hemiacetals.
 We also saw that cyclic hemiacetals form very
readily when hydroxyl and carbonyl groups are
part of the same molecule and that their
interaction produces a ring.
 Monosaccharides have hydroxyl and carbonyl
groups in the same molecule. As a result, they
exist almost exclusively as five- and six-
memberedcyclic hemiacetals.
 Haworth projection - a way to view furanose
and pyranose forms of monosaccharides;
 the ring is drawn flat and viewed through its
edge, with the anomeric carbon on the right
and the oxygen atom to the rear.
 Anomeric carbon- The hemiacetal carbon of the
cyclic form of a monosaccharide.
 Anomers - monosaccharides that differ in
configuration only at their anomeric carbons
 A common way of representing the cyclic
structure of monosaccharides is the Haworth
projection, named after the English chemist Sir
Walter N. Haworth (Nobel Prize in Chemistry,
1937).
 The new carbon stereocenter created in
forming the cyclic structure is called an
anomeric carbon.
 Stereoisomers that differ in configuration only
at the anomeric carbon are called anomers.
 The anomeric carbon of an aldose is carbon 1;
that of the most common ketoses is carbon 2.
 The designation ß means that the -OH on the
anomeric carbon of the cyclic hemiacetal
lies on the same side of the ring as the
terminal —CHOH.
 Conversely, the designation α means that
the -OH on the anomeric carbon of the cyclic
hemiacetal, lies on the side of the ring
opposite the terminal —CH OH.
 A six-membered hemiacetal ring is indicated
by -pyran-, and a five-membered hemiacetal
ring is indicated by -furan-.
 Aldopentoses also form cyclic hemiacetals.
 The most prevalent forms of D-ribose and
other pentoses in the biological world are
furanoses.
 The prefix 2-deoxy indicates the absence of
oxygen at carbon 2.
 Units of D-ribose and 2-deoxy-D-ribose in
nucleic acids and most other biological
molecules are found almost exclusively the in
the ß configuration.
 Fructose also forms five-membered cyclic
hemiacetals. β-D-fructofuranose for example, is
found in the disaccharide sucrose.
 For pyranoses, however, the six-membered
ring is more accurately represented as a chair
conformation.
 Mutarotation - the change in specific rotation
that occurs when an α or β form of a
carbohydrate is converted to an
equilibriummixture of the two forms.
 Mutarotation is the change in specific rotation
that accompanies the equilibration of a and B
anomers in aqueous solution.
 Mutarotation is common to all carbohydrates
that exist in hemiacetal forms.
 A cyclic-acetal derived from a monosaccharide
is called a glycoside, and from the anomeric
carbon to the —OR group is called a glycosidic
bond.
 Mutarotation is not possible in a glycoside
because an acetal-unlike anomeric carbon is
replaced with hemiacetal—is no longer in
equilibrium with the open-chain
carbonylcontaining compound.
 We name glycosides by listing the alkyl or aryl
group bonded to oxygen, followed by the name
of the carbohydrate in which the ending -e is
replaced with-ide.
 For example, the methyl glycoside derived from
B-D-glucopyranose is named methyl B-D-
glucopyranoside;
 Alditols - the products formed when the
CHOgroup of a monosaccharide is reduced to a
CH2OH group
 Sorbitol is found in the plant world in many
berries and in cherries, plums, pears, apples,
seaweed, and algae.
 used in the manufacture of candies and as a
sugar substitute for diabetics.
 Other alditols commonly found in the biological
world include erythritol, D-mannitol, and
xylitol.
 Xylitol is used as a sweetening agent in
"sugarless” gum, candy, and sweet cereals.
 Carbohydrate that reacts with a mild oxidizing
agent to form an acid is classified as a reducing
sugar
 Glucuronic acid is widely distributed in both the
plant and animal worlds.
 In humans, it serves as an important
component of the acidic polysaccharides of
connective tissues
 Mono- and diphosphoric esters are important
intermediates in the metabolism of
monosaccharides.
 Most carbohydrates in nature contain more
than one monosaccharide unit.
 Those that contain two-units are called
disaccharides, those that contain three units
are called trisaccharides, and so forth.
 We use the general termoligosaccharide to
describe carbohydrates that contain from six to
ten monosaccharide units.
 Carbohydrates containing larger numbers of
monosaccharide units are called
polysaccharides.
 In a disaccharide, two monosaccharide units are
joined by a glycosidic bond between the
anomeric carbon of one unit and an -OH group
of the other unit.
 Three important disaccharides are sucrose,
lactose, and maltose.
 Sucrose (table sugar) is the most abundant
disaccharide in the biological world.
 It is obtained principally from the juice of
sugarcane and sugar wan beets.
 Sucrose is a nonreducing sugar.
 Lactose is the principal sugar present in milk.
 Lactose is a reducing sugar, because the cyclic
hemiacetal of the D-glucopyranose unit is in
equilibrium with its open-chain form and can
be oxidized to a carboxyl group.
 Maltosederives its name from its presence in
malt, the juice from sprouted barley and other
cereal grains. Maltose is a reducing sugar
 Among the common sweetening agents, D-
fructose tastes the sweetest even sweeter
than sucrose
 The sweet taste of honey is due largely to D-
fructose and D-glucose.
 Lactose has almost no sweetness and is
sometimes added to foods as a filler.
 Polysaccharides consist of large numbers of
monosaccharide units bonded together by
glycosidic bonds.
 Three important polysaccharides, all made up
of glucose units, are starch, glycogen, and
cellulose.
 Starch is used for energy storage in plants.
 It is found in all plant seeds and tubers and is
the form in which glucose is stored for later use.
 Starch can be separated into two principal
polysaccharides: amylose and amylopectin.
  Complete hydrolysis of both amylose and
amylopectin yields only D-glucose.
 Amylose is composed of continuous,
unbranched chains of as many as 4000 D-
glucose units joined by a-1,4-glycosidic bonds.
 Amylopectin contains chains of as many as
10,000D-glucose units also joined by a-
1,4glycosidic bonds.
 Glycogen acts as the energy-reserve
carbohydrate for animals.
 The total amount of glycogen in the body of a
well-nourished adult human is about 350 g,
divided almost equally between liver and
muscle cells.
 Cellulose is a linear polysaccharide containing
as many as 3000 units of D-glucose joined by B-
1,4-glycosidic bonds.
 Cellulose, the most widely distributed plant
skeletal polysaccharide, constitutes almost half
of the cell-wall material of wood. Cotton is
almost pure cellulose.
 Cellulose molecules act much like stiff rods,
 Humans and other animals cannot use cellulose
as food because our digestive systems do not
contain B-glucosidases, enzymes that catalyze
the hydrolysis of B-glucosidic bonds.
 Instead, we have only a-glucosidases; hence,
we use the polysaccharides starch and glycogen
as sources of glucose.
that i. with collagen to form tight or loose
networks.
 Hyaluronic Acid is the simplest acidic
polysaccharide present in connective tissue.
 It is most abundant in embryonic tissues and in
specialized connective tissues such as synovial
fluid, the lubricant of joints in the body, and the
vitreous of the eye, where it provides a clear,
elastic gel that holds the retina in its proper
position.
 Hyaluronic acid is also a common ingredientin
lotions, moisturizers, and cosmetics.
 Heparin is a heterogeneous mixture of variably
sulfonated polysaccharide chains, ranging in
molecular weight from 6000 to 30,000 g/mol.
 This acidic polysaccharide is synthesized and
stored in mast cells (cells that are part of the
immune system and that occur in several types
of tissues) of various tissues—particularly the
liver, lungs, and gut.
 Heparin has many biological functions, the best
known and fully understood of which is its
anticoagulant activity.

20-6 What Are Acidic Polysaccharides?

 Acidic polysaccharides are a group of
polysaccharides that contain carboxyl groups
and/or sulfuric ester groups.
 Acidic polysaccharides play important roles in
the structure and function ofconnective
tissues.
 Because they contain amino sugars, a more
current name for these substances is
glycosaminoglycans.
 There is no single general type of connective
tissue. Rather, a large number of highly
specialized forms exist, such as cartilage, bone,
sy. novial fluid, skin, tendons, blood vessels,
intervertebral disks, and corned, Most
connective tissues consist of collagen, a
structural protein, combine with a variety of
acidic polysaccharides (glycosaminoglycans)